just booked a vacation in
iTrip.net®
  • Log In
  • START A FRANCHISE
  • Destinations
  • Vacation Deals
  • List Your Property
  • Blog
  • Contact us
  1. USA
  2. FL
  3. Lower Florida Keys
  4. Key West
  5. Lower Florida Keys

Properties in Key West
(76 reviews)

Showing all properties. Taxes & fees included.
Occupancy Options
SuMoTuWeThFrSa
27282930123456789101112131415161718192021222324252627282930311234567
SuMoTuWeThFrSa
27282930123456789101112131415161718192021222324252627282930311234567
 
Property Type
Amenities
Reset
Filter by Neighborhood
Big Pine Key (9) Cudjoe Key (9) Monthly Rentals (43) Ramrod Key (3) Sugarloaf Key (6) Summerland Key (4) Torch Keys (1)
 View Favorites
$17279 month
Location: Key West
Rating: 5 Stars
Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oasis and Private Pool!
6 Beds
4.5 Baths
Sleeps 10
$9696 month
Location: Key West
Rating: 5 Stars
Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapid Open Water Access!
4 Beds
2 Baths
Sleeps 6
$10840 month
Location: Key West
Rating: 5 Stars
Paradise: Beautifully Updated Conch Home, Pool, Quiet But Close Enough To Walk To Duval St & Beach!
3 Beds
3 Baths
Sleeps 6
$11894 month
Location: Key West
Anchors Aweigh: Stunning Oceanfront Views, Dockage, Private Pool, Tiki Hut, Spacious & Dog-Friendly!
5 Beds
2 Baths
Sleeps 10
$8025 month
Location: Key West
Rating: 4.5 Stars
Casa Cudjoe: Tropical Canal Front Retreat on Cudjoe Key, Dockage, Boater's Paradise & Dog-Friendly!
4 Beds
2 Baths
Sleeps 6
$7974 month
Location: Key West
Big Pine Paradise: Beautiful Updated 4BR Canal Front Home, Pool, Dockage, Easy Gulf/Atlantic Access
5 Beds
3 Baths
Sleeps 8
$6920 month
Location: Key West
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
6 Beds
2 Baths
Sleeps 10
$7920 month
Location: Key West
Rating: 5 Stars
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
5 Beds
2 Baths
Sleeps 8
$9678 month
Location: Key West
Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water Views & Boat Dockage!
4 Beds
2.5 Baths
Sleeps 6
$5224 month
Location: Key West
Tropical Tee-Time: 2BR Townhome in Key West Golf Club with Two Shared Pools, Fitness Center, Dogs OK
2 Beds
1.5 Baths
Sleeps 4
$7866 month
Location: Key West
Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beaches & Duval Street!
3 Beds
2 Baths
Sleeps 6
$7554 month
Location: Key West
Summerland Sanctuary: 3BR Canal Front Retreat with Private Pool, Dockage & Premier Boating/Fishing
5 Beds
2 Baths
Sleeps 8
  • 1
  • 2
  • 3
  • 4
  • 5
  • Next
Connect With Us
Vacation Rentals Vacation Destinations Vacation Deals View Favorites
About iTrip Blog Contact Us About Reviews Guarantee FAQ Privacy Policy
Translate   Choose Language
Property Management List Your Property Owner FAQ Benefits Franchises
VRBO Airbnb Flipkey
Copyright © 2008 - 2025 iTrip LLC